NP-MRD: Showing NP-Card for Glabramycin A (NP0008426)

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Record Information

Version

2.0

Created at

2020-12-09 06:01:16 UTC

Updated at

2021-07-15 17:00:23 UTC

NP-MRD ID

NP0008426

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Glabramycin A

Provided By

NPAtlas

Description

(2E,4E,6E)-8-hydroxy-8-[(1E)-9-hydroxy-4-methyl-2-oxo-2,4,5,6,7,8-hexahydro-1H-3-benzoxecin-1-ylidene]octa-2,4,6-trienoic acid belongs to the class of organic compounds known as oxocins. Oxocins are compounds containing an oxocin ring, which is a eight-member unsaturated aromatic ring containing one oxygen atom and seven carbon atoms. Glabramycin A is found in Neosartorya. Glabramycin A was first documented in 2009 (PMID: 19343064). Based on a literature review very few articles have been published on (2E,4E,6E)-8-hydroxy-8-[(1E)-9-hydroxy-4-methyl-2-oxo-2,4,5,6,7,8-hexahydro-1H-3-benzoxecin-1-ylidene]octa-2,4,6-trienoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106103D          

 52 53  0  0  0  0            999 V2000
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   -1.9589   -2.0121    1.1400 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0874   -2.5130    0.2582 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1919   -1.5393    0.0767 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8343   -0.1382    0.4358 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.6504    1.8776   -0.3487 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 52 53  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306242106103D          

 52 53  0  0  0  0            999 V2000
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   -4.0288    5.0174   -0.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6824    5.4974    0.5899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0729    3.7684    0.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6277    3.5110   -0.9047 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0825   -0.1383   -0.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9995    2.3039   -1.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0999    1.5234   -1.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9525    0.0636   -1.8930 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6472   -2.1358   -0.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3282   -1.6252   -1.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0568   -3.9080    0.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 14 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28  2  1  0  0  0  0
 13  7  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  2 32  1  1  0  0  0
  3 33  1  0  0  0  0
  3 34  1  0  0  0  0
  4 35  1  0  0  0  0
  4 36  1  0  0  0  0
  5 37  1  0  0  0  0
  5 38  1  0  0  0  0
  6 39  1  0  0  0  0
  6 40  1  0  0  0  0
  9 41  1  0  0  0  0
 10 42  1  0  0  0  0
 11 43  1  0  0  0  0
 12 44  1  0  0  0  0
 16 45  1  0  0  0  0
 17 46  1  0  0  0  0
 18 47  1  0  0  0  0
 19 48  1  0  0  0  0
 20 49  1  0  0  0  0
 21 50  1  0  0  0  0
 22 51  1  0  0  0  0
 25 52  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0008426

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C(\[H])=C(/[H])C([H])=C([H])C(\[H])=C(/[H])\C(\O[H])=C1\C2=C([H])C([H])=C([H])C(O[H])=C2C([H])([H])C([H])([H])C([H])([H])C([H])([H])[C@]([H])(OC1=O)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H24O6/c1-15-9-6-7-10-16-17(11-8-13-18(16)23)21(22(27)28-15)19(24)12-4-2-3-5-14-20(25)26/h2-5,8,11-15,23-24H,6-7,9-10H2,1H3,(H,25,26)/b3-2-,12-4+,14-5+,21-19+/t15-/m1/s1

> <INCHI_KEY>
JASBGADMEMUKAU-NMKCLXBBSA-N

> <FORMULA>
C22H24O6

> <MOLECULAR_WEIGHT>
384.428

> <EXACT_MASS>
384.157288493

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
42.30129267095491

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,6E)-8-hydroxy-8-[(1E,4R)-9-hydroxy-4-methyl-2-oxo-2,4,5,6,7,8-hexahydro-1H-3-benzoxecin-1-ylidene]octa-2,4,6-trienoic acid

> <ALOGPS_LOGP>
3.92

> <JCHEM_LOGP>
4.403805178666667

> <ALOGPS_LOGS>
-4.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.048459107828245

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.467804465355611

> <JCHEM_PKA_STRONGEST_BASIC>
-5.323966300883927

> <JCHEM_POLAR_SURFACE_AREA>
104.06000000000002

> <JCHEM_REFRACTIVITY>
110.1886

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,6E)-8-hydroxy-8-[(1E,4R)-9-hydroxy-4-methyl-2-oxo-5,6,7,8-tetrahydro-4H-3-benzoxecin-1-ylidene]octa-2,4,6-trienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 52 53  0  0  0  0  0  0  0  0999 V2000
   -1.1121   -3.2785    1.4124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9589   -2.0121    1.1400 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0874   -2.5130    0.2582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1919   -1.5393    0.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8343   -0.1382    0.4358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2007    0.5564   -0.7468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6504    1.8776   -0.3487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5929    2.9160   -0.3891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9071    2.6522   -0.7731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3022    4.2185   -0.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9982    4.4819    0.3143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0569    3.4906    0.3643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3542    2.1447    0.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2557    1.1818    0.0973 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8495    1.6389   -0.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8610    2.9109   -1.1623 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0360    0.8423   -0.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1227    1.3233   -1.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059    0.4588   -1.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1633   -0.3054   -1.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3956   -1.6058   -0.6302 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5774   -2.1861   -0.7822 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8736   -3.4858   -0.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0383   -3.9764   -0.4233 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9401   -4.2302    0.4692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2415   -0.1259    0.7717 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8643   -0.2787    1.4751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1832   -1.0245    0.6940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5605   -3.4554    0.4495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7852   -4.1252    1.5561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4239   -3.0961    2.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3508   -1.7673    2.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6364   -2.9184   -0.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5346   -3.4282    0.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4529   -1.5302   -1.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0928   -1.8820    0.6403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7847    0.3810    0.7392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2037   -0.1018    1.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0790    0.7121   -1.4646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4983   -0.0199   -1.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6073    3.3597   -0.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0288    5.0174   -0.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6824    5.4974    0.5899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0729    3.7684    0.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6277    3.5110   -0.9047 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0825   -0.1383   -0.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9995    2.3039   -1.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0999    1.5234   -1.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9525    0.0636   -1.8930 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6472   -2.1358   -0.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3282   -1.6252   -1.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0568   -3.9080    0.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 14 26  1  0
 26 27  2  0
 26 28  1  0
 28  2  1  0
 13  7  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  1
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  6 40  1  0
  9 41  1  0
 10 42  1  0
 11 43  1  0
 12 44  1  0
 16 45  1  0
 17 46  1  0
 18 47  1  0
 19 48  1  0
 20 49  1  0
 21 50  1  0
 22 51  1  0
 25 52  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.112  -3.279   1.412  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.959  -2.012   1.140  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.087  -2.513   0.258  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.192  -1.539   0.077  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.834  -0.138   0.436  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.201   0.556  -0.747  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.650   1.878  -0.349  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.593   2.916  -0.389  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.907   2.652  -0.773  0.00  0.00           O+0
HETATM   10  C   UNK     0      -3.302   4.218  -0.066  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.998   4.482   0.314  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.057   3.491   0.364  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.354   2.145   0.031  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.256   1.182   0.097  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.850   1.639  -0.537  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.861   2.911  -1.162  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.036   0.842  -0.594  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.123   1.323  -1.221  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.206   0.459  -1.206  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.163  -0.305  -1.193  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.396  -1.606  -0.630  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.577  -2.186  -0.782  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.874  -3.486  -0.242  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.038  -3.976  -0.423  0.00  0.00           O+0
HETATM   25  O   UNK     0       5.940  -4.230   0.469  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.242  -0.126   0.772  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.864  -0.279   1.475  0.00  0.00           O+0
HETATM   28  O   UNK     0      -1.183  -1.024   0.694  0.00  0.00           O+0
HETATM   29  H   UNK     0      -0.561  -3.455   0.450  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.785  -4.125   1.556  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.424  -3.096   2.266  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.351  -1.767   2.171  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.636  -2.918  -0.667  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.535  -3.428   0.753  0.00  0.00           H+0
HETATM   35  H   UNK     0      -4.453  -1.530  -1.023  0.00  0.00           H+0
HETATM   36  H   UNK     0      -5.093  -1.882   0.640  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.785   0.381   0.739  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.204  -0.102   1.353  0.00  0.00           H+0
HETATM   39  H   UNK     0      -4.079   0.712  -1.465  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.498  -0.020  -1.334  0.00  0.00           H+0
HETATM   41  H   UNK     0      -5.607   3.360  -0.817  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.029   5.017  -0.097  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.682   5.497   0.590  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.073   3.768   0.684  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.628   3.511  -0.905  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.083  -0.138  -0.176  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.999   2.304  -1.662  0.00  0.00           H+0
HETATM   48  H   UNK     0       5.100   1.523  -1.295  0.00  0.00           H+0
HETATM   49  H   UNK     0       5.952   0.064  -1.893  0.00  0.00           H+0
HETATM   50  H   UNK     0       4.647  -2.136  -0.083  0.00  0.00           H+0
HETATM   51  H   UNK     0       7.328  -1.625  -1.346  0.00  0.00           H+0
HETATM   52  H   UNK     0       5.057  -3.908   0.769  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    1    3   28   32                                             
CONECT    3    2    4   33   34                                             
CONECT    4    3    5   35   36                                             
CONECT    5    4    6   37   38                                             
CONECT    6    5    7   39   40                                             
CONECT    7    6    8   13                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8   41                                                       
CONECT   10    8   11   42                                                  
CONECT   11   10   12   43                                                  
CONECT   12   11   13   44                                                  
CONECT   13   12   14    7                                                  
CONECT   14   13   15   26                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   45                                                       
CONECT   17   15   18   46                                                  
CONECT   18   17   19   47                                                  
CONECT   19   18   20   48                                                  
CONECT   20   19   21   49                                                  
CONECT   21   20   22   50                                                  
CONECT   22   21   23   51                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   52                                                       
CONECT   26   14   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26    2                                                       
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    2                                                            
CONECT   33    3                                                            
CONECT   34    3                                                            
CONECT   35    4                                                            
CONECT   36    4                                                            
CONECT   37    5                                                            
CONECT   38    5                                                            
CONECT   39    6                                                            
CONECT   40    6                                                            
CONECT   41    9                                                            
CONECT   42   10                                                            
CONECT   43   11                                                            
CONECT   44   12                                                            
CONECT   45   16                                                            
CONECT   46   17                                                            
CONECT   47   18                                                            
CONECT   48   19                                                            
CONECT   49   20                                                            
CONECT   50   21                                                            
CONECT   51   22                                                            
CONECT   52   25                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  106    0
END

RDKit          3D

52 53  0  0  0  0  0  0  0  0999 V2000
   -1.1121   -3.2785    1.4124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9589   -2.0121    1.1400 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0874   -2.5130    0.2582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1919   -1.5393    0.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8343   -0.1382    0.4358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2007    0.5564   -0.7468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6504    1.8776   -0.3487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5929    2.9160   -0.3891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9071    2.6522   -0.7731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3022    4.2185   -0.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9982    4.4819    0.3143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0569    3.4906    0.3643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3542    2.1447    0.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2557    1.1818    0.0973 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8495    1.6389   -0.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8610    2.9109   -1.1623 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0360    0.8423   -0.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1227    1.3233   -1.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059    0.4588   -1.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1633   -0.3054   -1.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3956   -1.6058   -0.6302 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5774   -2.1861   -0.7822 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8736   -3.4858   -0.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0383   -3.9764   -0.4233 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9401   -4.2302    0.4692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2415   -0.1259    0.7717 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8643   -0.2787    1.4751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1832   -1.0245    0.6940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5605   -3.4554    0.4495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7852   -4.1252    1.5561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4239   -3.0961    2.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3508   -1.7673    2.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6364   -2.9184   -0.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5346   -3.4282    0.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4529   -1.5302   -1.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0928   -1.8820    0.6403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7847    0.3810    0.7392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2037   -0.1018    1.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0790    0.7121   -1.4646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4983   -0.0199   -1.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6073    3.3597   -0.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0288    5.0174   -0.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6824    5.4974    0.5899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0729    3.7684    0.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6277    3.5110   -0.9047 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0825   -0.1383   -0.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9995    2.3039   -1.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0999    1.5234   -1.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9525    0.0636   -1.8930 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6472   -2.1358   -0.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3282   -1.6252   -1.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0568   -3.9080    0.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 14 26  1  0
 26 27  2  0
 26 28  1  0
 28  2  1  0
 13  7  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  1
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  6 40  1  0
  9 41  1  0
 10 42  1  0
 11 43  1  0
 12 44  1  0
 16 45  1  0
 17 46  1  0
 18 47  1  0
 19 48  1  0
 20 49  1  0
 21 50  1  0
 22 51  1  0
 25 52  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2E,4E,6E)-8-Hydroxy-8-[(1E)-9-hydroxy-4-methyl-2-oxo-2,4,5,6,7,8-hexahydro-1H-3-benzoxecin-1-ylidene]octa-2,4,6-trienoate	Generator

Chemical Formula

C₂₂H₂₄O₆

Average Mass

384.4280 Da

Monoisotopic Mass

384.15729 Da

IUPAC Name

(2E,6E)-8-hydroxy-8-[(1E,4R)-9-hydroxy-4-methyl-2-oxo-2,4,5,6,7,8-hexahydro-1H-3-benzoxecin-1-ylidene]octa-2,4,6-trienoic acid

Traditional Name

(2E,6E)-8-hydroxy-8-[(1E,4R)-9-hydroxy-4-methyl-2-oxo-5,6,7,8-tetrahydro-4H-3-benzoxecin-1-ylidene]octa-2,4,6-trienoic acid

CAS Registry Number

Not Available

SMILES

CC1CCCCC2=C(C=CC=C2O)\C(=C(/O)\C=C\C=C\C=C\C(O)=O)C(=O)O1

InChI Identifier

InChI=1S/C22H24O6/c1-15-9-6-7-10-16-17(11-8-13-18(16)23)21(22(27)28-15)19(24)12-4-2-3-5-14-20(25)26/h2-5,8,11-15,23-24H,6-7,9-10H2,1H3,(H,25,26)/b3-2+,12-4+,14-5+,21-19+

InChI Key

JASBGADMEMUKAU-NMKCLXBBSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Neosartorya	NPAtlas	19343064

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxocins. Oxocins are compounds containing an oxocin ring, which is a eight-member unsaturated aromatic ring containing one oxygen atom and seven carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxocins

Sub Class

Not Available

Direct Parent

Oxocins

Alternative Parents

Substituents

Oxocin
Medium-chain fatty acid
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Heterocyclic fatty acid
Hydroxy fatty acid
Phenol
Dicarboxylic acid or derivatives
Unsaturated fatty acid
Fatty acyl
Benzenoid
Fatty acid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous acid
Lactone
Carboxylic acid ester
Carboxylic acid derivative
Oxacycle
Enol
Carboxylic acid
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.92	ALOGPS
logP	4.4	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	4.47	ChemAxon
pKa (Strongest Basic)	-5.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	110.19 m³·mol⁻¹	ChemAxon
Polarizability	42.3 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA019935

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28286374

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54728247

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jayasuriya H, Zink D, Basilio A, Vicente F, Collado J, Bills G, Goldman ML, Motyl M, Huber J, Dezeny G, Byrne K, Singh SB: Discovery and antibacterial activity of glabramycin A-C from Neosartorya glabra by an antisense strategy. J Antibiot (Tokyo). 2009 May;62(5):265-9. doi: 10.1038/ja.2009.26. Epub 2009 Apr 3. [PubMed:19343064 ]

Showing NP-Card for Glabramycin A (NP0008426)

MOL for NP0008426 (Glabramycin A)

3D MOL for NP0008426 (Glabramycin A)

3D SDF for NP0008426 (Glabramycin A)

3D-SDF for NP0008426 (Glabramycin A)

PDB for NP0008426 (Glabramycin A)

3D PDB for NP0008426 (Glabramycin A)

SMILES for NP0008426 (Glabramycin A)

INCHI for NP0008426 (Glabramycin A)

Structure for NP0008426 (Glabramycin A)

3D Structure for NP0008426 (Glabramycin A)